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Functional Conducting Polymers via Thiol-ene Chemistry.

Feldman KE, Martin DC - Biosensors (Basel) (2012)

Bottom Line: We demonstrate here that thiol-ene chemistry can be used to provide side-chain functionalized monomers based on 3,4-propylenedioxythiophene (ProDOT) containing ionic, neutral, hydrophobic, and hydrophilic side chains.These monomers were polymerized either chemically or electro-chemically to give soluble materials or conductive films, respectively.This strategy provides for facile tuning of the solubility, film surface chemistry, and film morphology of this class of conducting polymers.

View Article: PubMed Central - PubMed

Affiliation: Department of Materials Science and Engineering, University of Delaware, Newark, DE 19716, USA. katiefeldman0@gmail.com.

ABSTRACT
We demonstrate here that thiol-ene chemistry can be used to provide side-chain functionalized monomers based on 3,4-propylenedioxythiophene (ProDOT) containing ionic, neutral, hydrophobic, and hydrophilic side chains. All reactions gave high yields and purification could generally be accomplished through precipitation. These monomers were polymerized either chemically or electro-chemically to give soluble materials or conductive films, respectively. This strategy provides for facile tuning of the solubility, film surface chemistry, and film morphology of this class of conducting polymers.

No MeSH data available.


SEM micrographs of films electrochemically deposited from solutions of (A) 10% ProDOT-CO2H + 90% ProDOT; (B) 20% ProDOT-CO2H + 80% ProDOT; (C) 10% ProDOT-NH2 + 90% ProDOT; (D) 20% ProDOT-NH2 + 80% ProDOT; (E) 10% ProDOT-glycerol + 90% ProDOT; (F) 20% ProDOT-glycerol + 80% ProDOT; (G) 10% ProDOT-SO3Na + 90% ProDOT; (H) 20% ProDOT-SO3Na + 80% ProDOT and (I) ProDOT. Composition refers to the relative molar percentage in deposition solution. In all cases total monomer concentration was 50 mM in propylene carbonate with 100 mM TBAP as supporting electrolyte/counterion.
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biosensors-02-00305-f002: SEM micrographs of films electrochemically deposited from solutions of (A) 10% ProDOT-CO2H + 90% ProDOT; (B) 20% ProDOT-CO2H + 80% ProDOT; (C) 10% ProDOT-NH2 + 90% ProDOT; (D) 20% ProDOT-NH2 + 80% ProDOT; (E) 10% ProDOT-glycerol + 90% ProDOT; (F) 20% ProDOT-glycerol + 80% ProDOT; (G) 10% ProDOT-SO3Na + 90% ProDOT; (H) 20% ProDOT-SO3Na + 80% ProDOT and (I) ProDOT. Composition refers to the relative molar percentage in deposition solution. In all cases total monomer concentration was 50 mM in propylene carbonate with 100 mM TBAP as supporting electrolyte/counterion.

Mentions: The surface morphology of electrochemically deposited films has a significant effect on their redox properties; greater surface area tends to reduce electrochemical impedance, a critical property for applications in neural interfaces [36]. This is beneficial in devices such as neural prosthetics that critically rely on efficient charge transport across the film interface. Additionally, it has been shown that roughness can have a dramatic effect on the ability of cells to adhere to functional surfaces [37,38]. Scanning electron microscopy characterization of the electrochemically deposited films containing ProDOT-CO2H showed an increase in roughness with 10% comonomer in the feed (Figure 2(A)). At 20% comonomer (Figure 2(B)), the local roughness (on the submicron scale) decreased, but large bubbles of several to tens of microns in diameter were seen to cover most of the film. Incorporation of the carboxylic acid containing monomer into the film presumably allows it to swell in the deposition solution to a greater extent than pure ProDOT films, leading to bubbling as the film thickness increases. Similarly, large wrinkles were seen in films deposited from 10% ProDOT-glycerol solution (Figure 2(E)), and bubbles appeared in films deposited from 20% ProDOT-glycerol solution (Figure 2(F)). Films generated from ProDOT-NH2-containing solutions (Figure 2(C,D)) had a similar morphology to pure ProDOT films (Figure 2(I)), while ProDOT-SO3Na-containing films were relatively smooth (Figure 2(G,H)).


Functional Conducting Polymers via Thiol-ene Chemistry.

Feldman KE, Martin DC - Biosensors (Basel) (2012)

SEM micrographs of films electrochemically deposited from solutions of (A) 10% ProDOT-CO2H + 90% ProDOT; (B) 20% ProDOT-CO2H + 80% ProDOT; (C) 10% ProDOT-NH2 + 90% ProDOT; (D) 20% ProDOT-NH2 + 80% ProDOT; (E) 10% ProDOT-glycerol + 90% ProDOT; (F) 20% ProDOT-glycerol + 80% ProDOT; (G) 10% ProDOT-SO3Na + 90% ProDOT; (H) 20% ProDOT-SO3Na + 80% ProDOT and (I) ProDOT. Composition refers to the relative molar percentage in deposition solution. In all cases total monomer concentration was 50 mM in propylene carbonate with 100 mM TBAP as supporting electrolyte/counterion.
© Copyright Policy - open-access
Related In: Results  -  Collection

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getmorefigures.php?uid=PMC4263549&req=5

biosensors-02-00305-f002: SEM micrographs of films electrochemically deposited from solutions of (A) 10% ProDOT-CO2H + 90% ProDOT; (B) 20% ProDOT-CO2H + 80% ProDOT; (C) 10% ProDOT-NH2 + 90% ProDOT; (D) 20% ProDOT-NH2 + 80% ProDOT; (E) 10% ProDOT-glycerol + 90% ProDOT; (F) 20% ProDOT-glycerol + 80% ProDOT; (G) 10% ProDOT-SO3Na + 90% ProDOT; (H) 20% ProDOT-SO3Na + 80% ProDOT and (I) ProDOT. Composition refers to the relative molar percentage in deposition solution. In all cases total monomer concentration was 50 mM in propylene carbonate with 100 mM TBAP as supporting electrolyte/counterion.
Mentions: The surface morphology of electrochemically deposited films has a significant effect on their redox properties; greater surface area tends to reduce electrochemical impedance, a critical property for applications in neural interfaces [36]. This is beneficial in devices such as neural prosthetics that critically rely on efficient charge transport across the film interface. Additionally, it has been shown that roughness can have a dramatic effect on the ability of cells to adhere to functional surfaces [37,38]. Scanning electron microscopy characterization of the electrochemically deposited films containing ProDOT-CO2H showed an increase in roughness with 10% comonomer in the feed (Figure 2(A)). At 20% comonomer (Figure 2(B)), the local roughness (on the submicron scale) decreased, but large bubbles of several to tens of microns in diameter were seen to cover most of the film. Incorporation of the carboxylic acid containing monomer into the film presumably allows it to swell in the deposition solution to a greater extent than pure ProDOT films, leading to bubbling as the film thickness increases. Similarly, large wrinkles were seen in films deposited from 10% ProDOT-glycerol solution (Figure 2(E)), and bubbles appeared in films deposited from 20% ProDOT-glycerol solution (Figure 2(F)). Films generated from ProDOT-NH2-containing solutions (Figure 2(C,D)) had a similar morphology to pure ProDOT films (Figure 2(I)), while ProDOT-SO3Na-containing films were relatively smooth (Figure 2(G,H)).

Bottom Line: We demonstrate here that thiol-ene chemistry can be used to provide side-chain functionalized monomers based on 3,4-propylenedioxythiophene (ProDOT) containing ionic, neutral, hydrophobic, and hydrophilic side chains.These monomers were polymerized either chemically or electro-chemically to give soluble materials or conductive films, respectively.This strategy provides for facile tuning of the solubility, film surface chemistry, and film morphology of this class of conducting polymers.

View Article: PubMed Central - PubMed

Affiliation: Department of Materials Science and Engineering, University of Delaware, Newark, DE 19716, USA. katiefeldman0@gmail.com.

ABSTRACT
We demonstrate here that thiol-ene chemistry can be used to provide side-chain functionalized monomers based on 3,4-propylenedioxythiophene (ProDOT) containing ionic, neutral, hydrophobic, and hydrophilic side chains. All reactions gave high yields and purification could generally be accomplished through precipitation. These monomers were polymerized either chemically or electro-chemically to give soluble materials or conductive films, respectively. This strategy provides for facile tuning of the solubility, film surface chemistry, and film morphology of this class of conducting polymers.

No MeSH data available.